Réaction #1726671

ord-082ecab26f0a42cfaf1b23d805743005

Équation de réaction

C=C[C@H]1CN2CC[C@H]1C[C@H]2[C@H](O)c1ccnc2ccccc12
(−) cinchonidine
[H][H]
hydrogen
COC(=O)C(=O)c1ccccc1
methyl benzoyl formate
→
COC(=O)[C@H](O)c1ccccc1
(R)-methyl mandelate
Rendement 88.5%

Réactifs

C=C[C@H]1CN2CC[C@H]1C[C@H]2[C@H](O)c1ccnc2ccccc12
(−) cinchonidine
—
Ir
—
Example 10
[H][H]
hydrogen
COC(=O)C(=O)c1ccccc1
methyl benzoyl formate

Réactifs

Aucun

Solvants

Cc1ccccc1
toluene

Conditions de réaction

Conditions détaillées
See reaction.notes.procedure_details.

Traitement

  1. 1
    workup.ADDITIONwere mixed in an autoclave
  2. 2
    Autrewas removed by filtration
  3. 3
    Autreafter the reaction
  4. 4
    ConcentrationThe filtrate was concentrated
  5. 5
    Autrethe residue was purified

Mode opératoire

The cross-linked Ir cluster composition obtained in Example 10 (14.4 mg, 0.01 mmole), methyl benzoyl formate (164.2 mg, 1.0 mmole), (−) cinchonidine (3.8 mg, 0.013 mmole) and toluene (5 ml) were mixed in an autoclave and agitated for five hours at room temperature in a hydrogen atmosphere at 50 atmospheres pressure. The cross linked Ir cluster composition was removed by filtration after the reaction. The filtrate was concentrated, and the residue was purified using PTLC to obtain (R)-methyl mandelate (147.1 mg, 88.5% yield). The asymmetric yield was 47.1% ee.

Source

DOI: 10.6084/m9.figshare.5104873.v1Brevet: US08110519B2uspto-grants-2012_02